If you are not selling your home - check to see how renting it out may affect your ability to get financing. The way they calculate rent - and qualify you has become more stringent over the last year.
If you can afford to do so - and your home in Boston is in a good neighborhood - why not keep it? Generally - it is better to sell when the market is strong. A few years down the road may be a better time.
I lived in Annapolis for years and know it well. You will LOVE the area and surrounds. If you need assistance - feel free to contact me,